tert-Butanol → tert-Butyl 4-(6-bromo-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate

HRID 2205866노트

반응식

HRID 2205866 반응식
C1CCN2C(=NCCC2)CC1.[Br:12][C:13]1[N:18]=[CH:17][C:16]2[CH:19]=[C:20]([C:26]3[CH:27]=[N:28][N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:30]=3)[N:21](S(C)(=O)=O)[C:15]=2[CH:14]=1.C(O)(C)(C)C>C1COCC1.O>[Br:12][C:13]1[N:18]=[CH:17][C:16]2[CH:19]=[C:20]([C:26]3[CH:27]=[N:28][N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:30]=3)[NH:21][C:15]=2[CH:14]=1

참가 물질

6

반응물 3

HCID 6386tert-ButanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86706269tert-Butyl 4-(6-bromo-1-(methylsulfonyl)-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate

생성물 1

HCID 86706280tert-Butyl 4-(6-bromo-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate수율 63.7%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
40 °C

실험 절차

DBU (0.193 mL, 1.289 mmol) was added to a solution of tert-butyl 4-(6-bromo-1-(methylsulfonyl)-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate (9) (0.517 g, 1.172 mmol) and tert-butanol (0.224 mL, 2.343 mmol) in THF (11.7 mL). The reaction mixture was stirred at 40° C. for 1 hr. It was then diluted with water and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude mixture was adsorbed on silica and purified via Biotage (DCM/EtOAc, 95/5 to 85/15, 25+M column) to afford the title compound as a white solid (271 mg, 58%). 1H NMR (500 MHz, CDCl3) 1.71 (s, 9H), 6.75 (s, 1H), 7.50 (s, 1H), 8.02 (s, 1H), 8.38 (s, 1H), 8.50 (s, 1H), 8.66 (s, 1H).

후처리

  1. extractionthe aqueous layer was extracted with EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. custompurified via Biotage (DCM/EtOAc, 95/5 to 85/15, 25+M column)

출처 및 근거

ORD 기록
ord-ba29c29b62234ba08b2c667cebdb8020
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371319B2

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